Detailed information for compound 1414468

Basic information

Technical information
  • TDR Targets ID: 1414468
  • Name: N-[4-[2-(4-hydroxyphenyl)-1,3-dioxoisoindol-5 -yl]oxyphenyl]thiophene-2-carboxamide
  • MW: 456.47 | Formula: C25H16N2O5S
  • H donors: 2 H acceptors: 4 LogP: 4.48 Rotable bonds: 6
    Rule of 5 violations (Lipinski): 1
  • SMILES: Oc1ccc(cc1)N1C(=O)c2c(C1=O)cc(cc2)Oc1ccc(cc1)NC(=O)c1cccs1
  • InChi: 1S/C25H16N2O5S/c28-17-7-5-16(6-8-17)27-24(30)20-12-11-19(14-21(20)25(27)31)32-18-9-3-15(4-10-18)26-23(29)22-2-1-13-33-22/h1-14,28H,(H,26,29)
  • InChiKey: ZRMKNWYOYJXOFR-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • N-[4-[2-(4-hydroxyphenyl)-1,3-dioxo-isoindolin-5-yl]oxyphenyl]thiophene-2-carboxamide
  • N-[4-[[2-(4-hydroxyphenyl)-1,3-dioxo-5-isoindolinyl]oxy]phenyl]-2-thiophenecarboxamide
  • N-[4-[2-(4-hydroxyphenyl)-1,3-diketo-isoindolin-5-yl]oxyphenyl]thiophene-2-carboxamide
  • N-[4-[2-(4-hydroxyphenyl)-1,3-dioxo-isoindol-5-yl]oxyphenyl]thiophene-2-carboxamide
  • MLS000553586
  • SMR000172103
  • Thiophene-2-carboxylic acid {4-[2-(4-hydroxy-phenyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yloxy]-phenyl}-amide
  • STK299876
  • Oprea1_325331
  • ZINC00838324
  • Oprea1_856916
  • BAS 02225105

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens ATPase family, AAA domain containing 5 Starlite/ChEMBL No references
Escherichia coli penicillin-binding protein Starlite/ChEMBL No references
Homo sapiens nuclear factor, erythroid 2-like 2 Starlite/ChEMBL No references
Homo sapiens microtubule-associated protein tau Starlite/ChEMBL No references
Epstein-Barr virus (strain B95-8) (HHV-4) (Human herpesvirus 4) Epstein-Barr nuclear antigen 1 Starlite/ChEMBL No references

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma mansoni microtubule-associated protein tau Get druggable targets OG5_133504 All targets in OG5_133504
Mycobacterium tuberculosis Possible penicillin-binding protein Get druggable targets OG5_149948 All targets in OG5_149948
Echinococcus granulosus microtubule associated protein 2 Get druggable targets OG5_133504 All targets in OG5_133504
Echinococcus multilocularis microtubule associated protein 2 Get druggable targets OG5_133504 All targets in OG5_133504
Schistosoma japonicum ko:K04380 microtubule-associated protein tau, putative Get druggable targets OG5_133504 All targets in OG5_133504
Echinococcus multilocularis atpase aaa+ type core atpase aaa type core Get druggable targets OG5_139225 All targets in OG5_139225
By sequence similarity to non orthologous known druggable targets
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Leishmania major ribonucleoside-diphosphate reductase small chain, putative 0.0076 0.0288 0.0255
Mycobacterium ulcerans esterase/lipase LipP 0.0043 0.0129 0.0144
Schistosoma mansoni transcription factor LCR-F1 0.0043 0.0129 0.007
Brugia malayi Bromodomain containing protein 0.0029 0.006 0.0026
Mycobacterium tuberculosis Possible conserved lipoprotein LpqK 0.0043 0.0129 0.0149
Onchocerca volvulus Alhambra homolog 0.0029 0.006 0.2736
Loa Loa (eye worm) MH2 domain-containing protein 0.0119 0.0493 0.0489
Loa Loa (eye worm) PHD-finger family protein 0.0029 0.006 0.0055
Echinococcus granulosus Basic leucine zipper bZIP transcription 0.0043 0.0129 0.007
Echinococcus granulosus Transcription factor JmjC domain containing protein 0.0095 0.0378 0.0321
Plasmodium vivax ribonucleotide reductase small subunit, putative 0.0026 0.0044 0.004
Onchocerca volvulus 0.0043 0.0129 1
Loa Loa (eye worm) beta-LACTamase domain containing family member 0.0043 0.0129 0.0124
Mycobacterium tuberculosis Probable fatty-acid-CoA ligase FadD2 (fatty-acid-CoA synthetase) (fatty-acid-CoA synthase) 0.0024 0.0033 0.0039
Mycobacterium tuberculosis Probable hydrolase 0.0043 0.0129 0.0149
Mycobacterium leprae RIBONUCLEOSIDE-DIPHOSPHATE REDUCTASE (BETA CHAIN) NRDF (RIBONUCLEOTIDE REDUCTASE SMALL SUBUNIT) (R2F PROTEIN) 0.0026 0.0044 0.0013
Loa Loa (eye worm) hypothetical protein 0.0043 0.0129 0.0124
Loa Loa (eye worm) hypothetical protein 0.0043 0.0129 0.0124
Mycobacterium tuberculosis Probable esterase LipL 0.0043 0.0129 0.0149
Schistosoma mansoni ribonucleoside-diphosphate reductase alpha subunit 0.2092 1 1
Loa Loa (eye worm) hypothetical protein 0.0024 0.0033 0.0029
Loa Loa (eye worm) hypothetical protein 0.0024 0.0033 0.0029
Mycobacterium tuberculosis Fatty-acid-AMP ligase FadD30 (fatty-acid-AMP synthetase) (fatty-acid-AMP synthase) 0.0018 0.0005 0.0005
Trypanosoma brucei ribonucleoside-diphosphate reductase large chain 0.2092 1 1
Entamoeba histolytica hypothetical protein 0.0043 0.0129 1
Mycobacterium tuberculosis Probable ribonucleoside-diphosphate reductase (large subunit) NrdZ (ribonucleotide reductase) 0.0651 0.3058 0.3536
Plasmodium vivax ribonucleoside-diphosphate reductase small chain, putative 0.0076 0.0288 0.0283
Echinococcus granulosus microtubule associated protein 2 0.0833 0.3935 0.3898
Mycobacterium tuberculosis Ribonucleoside-diphosphate reductase (beta chain) NrdB (ribonucleotide reductase small chain) 0.0076 0.0288 0.0333
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription 0.0043 0.0129 0.007
Mycobacterium tuberculosis Conserved protein 0.0043 0.0129 0.0149
Trypanosoma cruzi ribonucleoside-diphosphate reductase small chain, putative 0.0076 0.0288 0.0161
Echinococcus multilocularis microtubule associated protein 2 0.0833 0.3935 0.3898
Trypanosoma cruzi ribonucleoside-diphosphate reductase small chain, putative 0.0076 0.0288 0.0161
Trypanosoma cruzi ribonucleoside-diphosphate reductase large chain, putative 0.0556 0.2598 0.2501
Echinococcus multilocularis beta LACTamase domain containing family member 0.0043 0.0129 0.007
Mycobacterium tuberculosis Possible penicillin-binding protein 0.0278 0.1258 0.1454
Plasmodium vivax ribonucleoside-diphosphate reductase large chain, putative 0.2092 1 1
Mycobacterium ulcerans long-chain fatty-acid CoA ligase 0.0024 0.0033 0.0033
Echinococcus multilocularis atpase aaa+ type core atpase aaa type core 0.0979 0.4638 0.4606
Mycobacterium tuberculosis Probable lipase LipE 0.0043 0.0129 0.0149
Schistosoma mansoni microtubule-associated protein tau 0.0833 0.3935 0.3898
Echinococcus multilocularis ribonucleoside diphosphate reductase subunit 0.0076 0.0288 0.0229
Entamoeba histolytica hypothetical protein 0.0043 0.0129 1
Loa Loa (eye worm) hypothetical protein 0.0024 0.0033 0.0029
Loa Loa (eye worm) hypothetical protein 0.0029 0.006 0.0055
Plasmodium falciparum ribonucleoside-diphosphate reductase small chain, putative 0.0026 0.0044 0.004
Mycobacterium leprae conserved hypothetical protein 0.028 0.127 0.1435
Chlamydia trachomatis ribonucleoside-diphosphate reductase subunit beta 0.0076 0.0288 0.0283
Brugia malayi beta-lactamase family protein 0.0043 0.0129 0.0096
Plasmodium falciparum ribonucleoside-diphosphate reductase large subunit, putative 0.2092 1 1
Brugia malayi beta-lactamase family protein 0.0043 0.0129 0.0096
Plasmodium vivax hypothetical protein, conserved 0.0029 0.006 0.0055
Mycobacterium ulcerans long-chain-fatty-acid-CoA ligase 0.0024 0.0033 0.0033
Trichomonas vaginalis ribonucleoside-diphosphate reductase alpha chain, putative 0.1812 0.865 1
Loa Loa (eye worm) hypothetical protein 0.0043 0.0129 0.0124
Echinococcus granulosus ribonucleoside diphosphate reductase large 0.2092 1 1
Chlamydia trachomatis ribonucleoside-diphosphate reductase subunit alpha 0.2092 1 1
Leishmania major ribonucleoside-diphosphate reductase large chain, putative 0.2092 1 1
Giardia lamblia PHD finger protein 15 0.0029 0.006 0.5
Loa Loa (eye worm) transcription factor SMAD2 0.0119 0.0493 0.0489
Mycobacterium tuberculosis Probable conserved lipoprotein 0.0043 0.0129 0.0149
Loa Loa (eye worm) beta-lactamase 0.0043 0.0129 0.0124
Trypanosoma brucei ribonucleoside-diphosphate reductase small chain 0.0076 0.0288 0.0244
Echinococcus multilocularis ribonucleoside diphosphate reductase large 0.2092 1 1
Trypanosoma brucei hypothetical protein, conserved 0.0043 0.0129 0.0085
Toxoplasma gondii ribonucleoside-diphosphate reductase small subunit 0.0076 0.0288 0.0229
Mycobacterium tuberculosis Probable transcriptional regulatory protein NrdR 0.028 0.127 0.1468
Mycobacterium leprae Probable lipase LipE 0.0043 0.0129 0.0111
Leishmania major ribonucleoside-diphosphate reductase small chain, putative 0.0076 0.0288 0.0255
Loa Loa (eye worm) ribonucleoside-diphosphate reductase large subunit 0.2092 1 1
Plasmodium falciparum ribonucleoside-diphosphate reductase small chain, putative 0.0076 0.0288 0.0283
Schistosoma mansoni hypothetical protein 0.0043 0.0129 0.007
Loa Loa (eye worm) hypothetical protein 0.0043 0.0129 0.0124
Mycobacterium ulcerans lipase LipD 0.0043 0.0129 0.0144
Loa Loa (eye worm) hypothetical protein 0.005 0.016 0.0155
Schistosoma mansoni jumonji/arid domain-containing protein 0.0035 0.0089 0.003
Mycobacterium tuberculosis Conserved protein 0.0043 0.0129 0.0149
Brugia malayi hypothetical protein 0.0043 0.0129 0.0096
Trypanosoma cruzi ribonucleoside-diphosphate reductase large chain, putative 0.2092 1 1
Mycobacterium tuberculosis Probable esterase/lipase LipP 0.0043 0.0129 0.0149
Loa Loa (eye worm) hypothetical protein 0.0043 0.0129 0.0124
Brugia malayi jmjC domain containing protein 0.0095 0.0378 0.0346
Brugia malayi jmjC domain containing protein 0.0035 0.0089 0.0056
Schistosoma mansoni family S12 unassigned peptidase (S12 family) 0.0043 0.0129 0.007
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.0033 0.0033
Mycobacterium ulcerans ribonucleotide-diphosphate reductase subunit alpha 0.1812 0.865 1
Brugia malayi Hypothetical 52.5 kDa protein ZK945.1 in chromosome II, putative 0.0043 0.0129 0.0096
Mycobacterium ulcerans transcriptional regulator NrdR 0.028 0.127 0.1464
Mycobacterium ulcerans hypothetical protein 0.0024 0.0033 0.0033
Mycobacterium tuberculosis Ribonucleoside-diphosphate reductase (alpha chain) NrdE (ribonucleotide reductase small subunit) (R1F protein) 0.1812 0.865 1
Schistosoma mansoni family S12 unassigned peptidase (S12 family) 0.0043 0.0129 0.007
Mycobacterium tuberculosis Ribonucleoside-diphosphate reductase (beta chain) NrdF1 (ribonucleotide reductase small subunit) (R2F protein) 0.0076 0.0288 0.0333
Mycobacterium tuberculosis Conserved protein 0.0043 0.0129 0.0149
Echinococcus multilocularis lysine specific demethylase 5A 0.0035 0.0089 0.003
Mycobacterium ulcerans ribonucleotide-diphosphate reductase subunit beta 0.0026 0.0044 0.0046
Schistosoma mansoni ribonucleoside-diphosphate reductase small chain 0.0076 0.0288 0.0229
Echinococcus granulosus lysine specific demethylase 5A 0.0035 0.0089 0.003
Chlamydia trachomatis transcriptional repressor NrdR 0.028 0.127 0.1266
Onchocerca volvulus 0.0043 0.0129 1
Toxoplasma gondii ABC1 family protein 0.0043 0.0129 0.007
Trypanosoma brucei ribonucleoside-diphosphate reductase small chain, putative 0.0076 0.0288 0.0244
Plasmodium falciparum phd finger protein, putative 0.0029 0.006 0.0055
Brugia malayi PHD-finger family protein 0.0029 0.006 0.0026
Mycobacterium ulcerans fatty-acid-CoA ligase 0.0024 0.0033 0.0033
Toxoplasma gondii ribonucleoside-diphosphate reductase large chain 0.2092 1 1
Echinococcus granulosus beta LACTamase domain containing family member 0.0043 0.0129 0.007
Mycobacterium leprae conserved hypothetical protein 0.0043 0.0129 0.0111
Brugia malayi beta-lactamase 0.0043 0.0129 0.0096
Loa Loa (eye worm) hypothetical protein 0.0043 0.0129 0.0124
Schistosoma mansoni jumonji domain containing protein 0.0076 0.0284 0.0226
Mycobacterium ulcerans fusion of enoyl-CoA hydratase, EchA21 and lipase, LipE 0.0043 0.0129 0.0144
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.0033 0.0033
Echinococcus granulosus jumonji domain containing protein 0.004 0.0114 0.0055
Echinococcus multilocularis Transcription factor, JmjC domain containing protein 0.0095 0.0378 0.0321
Plasmodium vivax hypothetical protein, conserved 0.0043 0.0129 0.0124
Trypanosoma brucei ribonucleoside-diphosphate reductase small chain 0.0076 0.0288 0.0244
Mycobacterium ulcerans hypothetical protein 0.0043 0.0129 0.0144
Trypanosoma brucei ribonucleoside-diphosphate reductase small chain 0.0076 0.0288 0.0244
Entamoeba histolytica hypothetical protein 0.0043 0.0129 1
Treponema pallidum ribonucleotide-diphosphate reductase subunit alpha 0.2092 1 1
Wolbachia endosymbiont of Brugia malayi ribonucleotide-diphosphate reductase subunit alpha 0.1812 0.865 1
Entamoeba histolytica hypothetical protein 0.0043 0.0129 1
Brugia malayi ribonucleotide reductase 2 0.0076 0.0288 0.0255
Schistosoma mansoni jumonji/arid domain-containing protein 0.0035 0.0089 0.003
Echinococcus granulosus ribonucleoside diphosphate reductase subunit 0.0076 0.0288 0.0229
Mycobacterium leprae RIBONUCLEOSIDE-DIPHOSPHATE REDUCTASE (ALPHA CHAIN) NRDE (RIBONUCLEOTIDE REDUCTASE SMALL SUBUNIT) (R1F PROTEIN) 0.1812 0.865 1
Mycobacterium ulcerans long-chain-fatty-acid--CoA ligase 0.0024 0.0033 0.0033
Brugia malayi MH2 domain containing protein 0.0119 0.0493 0.0461
Loa Loa (eye worm) jmjC domain-containing protein 0.0035 0.0089 0.0084
Loa Loa (eye worm) jmjC domain-containing protein 0.006 0.0209 0.0204
Mycobacterium tuberculosis Probable lipase LipD 0.0043 0.0129 0.0149
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.0033 0.0033
Mycobacterium tuberculosis Probable chain -fatty-acid-CoA ligase FadD13 (fatty-acyl-CoA synthetase) 0.0024 0.0033 0.0039
Onchocerca volvulus 0.0043 0.0129 1
Mycobacterium ulcerans beta-lactamase 0.0043 0.0129 0.0144
Echinococcus multilocularis jumonji domain containing protein 0.004 0.0114 0.0055
Leishmania major hypothetical protein, conserved 0.0043 0.0129 0.0096
Loa Loa (eye worm) ribonucleotide reductase M2 B 0.0076 0.0288 0.0283

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 15.092 um PUBCHEM_BIOASSAY: Fluorescence polarization-based biochemical high throughput dose response assay for inhibitors of the Epstein-Barr virus nuclear antigen 1 (EBNA-1). (Class of assay: confirmatory) [Related pubchem assays: 2292 (Confirmation (EBNA-1 inhibitors in triplicate)), 2328 (Counterscreen (ZTA inhibitors in triplicate)), 1955 (Summary (EBNA-1 inhibitors))] ChEMBL. No reference
IC50 (binding) > 111.248 um PUBCHEM_BIOASSAY: Counterscreen for inhibitors of EBNA-1: fluorescence polarization-based biochemical high throughput dose response assay to identify inhibitors of the Epstein-Barr virus-encoded protein, ZTA. (Class of assay: confirmatory) [Related pubchem assays: 2292 (Confirmation (EBNA-1 inhibitors in triplicate)), 2328 (Counterscreen (ZTA inhibitors in triplicate)), 1955 (Summary (EBNA-1 inhibitors))] ChEMBL. No reference
Potency (functional) = 3.9811 um PUBCHEM_BIOASSAY: qHTS Inhibitors of AmpC Beta-Lactamase (assay with detergent). (Class of assay: confirmatory) [Related pubchem assays: 1002 (Confirmation Concentration-Response Assay for Inhibitors of AmpC Beta-Lactamase (assay with detergent)), 585 (Promiscuous and Specific Inhibitors of AmpC Beta-Lactamase (assay without detergent) - a screen old NIH MLSMR collection), 584 (Promiscuous and Specific Inhibitors of AmpC Beta-Lactamase (assay with detergent) - a screen of the old NIH MLSMR collection), 1003 (Confirmation Cuvette-Based Assay for Inhibitors of AmpC Beta-Lactamase (assay with detergent))] ChEMBL. No reference
Potency (functional) 8.1995 uM PUBCHEM_BIOASSAY: qHTS screen for small molecules that inhibit ELG1-dependent DNA repair in human embryonic kidney (HEK293T) cells expressing luciferase-tagged ELG1. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID493107, AID493125] ChEMBL. No reference
Potency (functional) = 14.1254 um PUBCHEM_BIOASSAY: qHTS for Inhibitors of Tau Fibril Formation, Fluorescence Polarization. (Class of assay: confirmatory) [Related pubchem assays: 596 ] ChEMBL. No reference
Potency (functional) 14.581 uM PUBCHEM_BIOASSAY: Nrf2 qHTS screen for inhibitors. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID493153, AID493163, AID504648] ChEMBL. No reference
Potency (functional) 18.526 uM PUBCHEM_BIOASSAY: Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID488745, AID488752, AID488774, AID504848, AID504850] ChEMBL. No reference
Potency (functional) = 56.2341 um PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of Human alpha-Glucosidase as a Potential Chaperone Treatment of Pompe Disease. (Class of assay: confirmatory) [Related pubchem assays: 997 ] ChEMBL. No reference
Potency (functional) = 56.2341 um PUBCHEM_BIOASSAY: qHTS Assay for Activators of Human alpha-Glucosidase as a Potential Chaperone Treatment of Pompe Disease. (Class of assay: confirmatory) [Related pubchem assays: 1467, 2100, 2112, 1473, 1466 ] ChEMBL. No reference
Potency (functional) = 79.3772 um PUBCHEM_BIOASSAY: Confirmation of Inhibitors Targeting the Menin-MLL Interaction in MLL Related Leukemias: Confirmation in an HTRF (commercial TR-FRET) Assay using His-tagged menin and biotin-labeled MLL peptide. (Class of assay: confirmatory) [Related pubchem assays: 1768, 2076, 1766 ] ChEMBL. No reference
Potency (functional) = 79.4328 um PUBCHEM_BIOASSAY: Confirmation of Inhibitors Targeting the Menin-MLL Interaction in MLL Related Leukemias: Competition With Texas Red Labeled MLL-derived Mutant Peptide. (Class of assay: confirmatory) [Related pubchem assays: 1768, 2076, 1766 ] ChEMBL. No reference
Potency (functional) = 398.1072 um PUBCHEM_BIOASSAY: Confirmation of Inhibitors Targeting the Menin-MLL Interaction in MLL Related Leukemias: Competition With Fluorescein Labeled MLL-derived Peptide. (Class of assay: confirmatory) [Related pubchem assays: 1768, 1766, 2076 ] ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23

Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.

Annotated phenotypes:

We have no manually annotated phenotypes for this drug. What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by drugs, or by genetic manipulation of cells (e.g. gene knockouts or knockdowns) is manually curated from the literature. These descriptions help to describe the potential of the target for drug development. If no information is available for this gene or if the information is incomplete, this may mean that i) the papers containing this information either appeared after the curation effort for this organism was carried out or they were inadvertently missed by curators; or that ii) the curation effort for this organism has not yet started.
 
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.

External resources for this compound

Bibliographic References

No literature references available for this target.

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